A friend of Charlie and Alan's mother, Olivia is present when the two brothers arrive at their mothers house and it is soon revealed that Charlie and her had partaken in a previous sexual rendezvous. Needless to say Charlie ends up ruining the dinner and the couple are unable to rekindle their brief yet interesting romance. Classic Sheen.
Mia always held a special place in Charlie's heart. Their courtship began when Charlie used Jack and took him to a ballet class that the child had no intention of going to, and it blossomed until the two of them finally got engaged. This was the closest to marriage that Charlie ever got throughout the series but unfortunately they split up when he couldn't stop his cigar-smoking, beer-swilling, and meat-eating ways. Which is a shame because she is incredibly beautiful. Silly Charlie, silly.
Chelsea Christine Melini
Chelsea was the first woman that Charlie ever confessed his love to without being prodded, which we all know is a milestone in any man's life. Of course, Charlie only says it by accident but he is persistent in the fact that he meant it. They end up getting engaged but once again Charlie is unable to settle down with her and she ends up actually leaving him! Which, to be honest, is completely understandable.
Jenny McCarthy's cameo in "Two And A Half Men" is an impressive lesson in how to be a con-woman. She is able to trick Charlie into bed, which admittedly isn't the hardest thing ever, but then she attempts to con the entire Harper family out of millions of dollars but is thwarted when her husband perishes. Who would have thought that her master-plan would be ruined by Robert Wagner. The guy's normally a rock!
Rose is perennially lurking around Charlie and his home, and she is sure that he and her are meant to be together. After sleeping with her prior to the series opening, Charlie has to deal with her constant attempts to reconnect their love. She also has a pretty familiar father too, who is played by ex-president of the United States, Martin Sheen.
She is probably the reason why Charlie is single for so long. After Charlie approaches Mia's house to apologize to her, he meets Ginger, a dancer who likes to bet on sports, eat meat, smoke and drink. Basically, she's everything that Charlie is looking for in a mate, and it leads to Charlie doing what Charlie does best: sleeping with her. Sadly, no one has ever lived up to the standard that she set.
There are some places that you would never ever expect to be able to seduce the ladies. A morgue and a gay club being the primary places that come to mind but a hospital is certainly in that category too. Especially when you are getting a mole removed from your butt. But Charlie is able to do so and is even able to seduce the dermatologist who performed the operation on him. The classy bastard that he is.